ChemicalBook--->CAS DataBase List--->554-92-7

554-92-7

554-92-7 Structure

554-92-7 Structure
IdentificationBack Directory
[Name]

TRIMETHOBENZAMIDE HYDROCHLORIDE
[CAS]

554-92-7
[Synonyms]

tigan
ro2-9578
tiganhydrochloride
Trimethobenzamide HCL
LABOTEST-BB LT00772325
Tribenzagan Hydrochloride
TRIMETHOBENZAMIDE HYDROCHLORIDE
Trimethobenzamide HCl (Ro 2-9578)
TRIMETHOBENZAMIDEHYDROCHLORIDE,USP
Trimethobenzamide Hydrochloride (200 mg)
Trimethobenzamide Hydrochloride (500 mg)
TRIMETHOBENZAMIDE HYDROCHLORIDE USP/EP/BP
n-(p-(2-(dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxy-benzamidhydrochlori
N-([2-Dimethylaminoethoxy] benzyl)-3,4,5-trimethoxybenzamide hydrochloride
N-(4-(2-dimethylaminoethoxy)benzyl)-3,4,5-trimethoxybenzamide hydrochloride
4-(2-dimethylaminoethoxy)-n-(3,4,5-trimethoxybenzoyl)benzylaminehydrochlorid
n-(p-(2-(dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxybenzamidehydrochloride
n-(p-(2-(dimethylamino)ethoxy)-benzyl)-3,4,5-trimethoxybenzamidemonohydrochl
N-{{4-[2-(Dimethylamino)ethoxy]phenyl}methyl}-3,4,5-trimethoxybenzamide monohydrochloride
[EINECS(EC#)]

209-075-6
[Molecular Formula]

C21H29ClN2O5
[MDL Number]

MFCD00057999
[MOL File]

554-92-7.mol
[Molecular Weight]

424.92
Chemical PropertiesBack Directory
[Melting point ]

187.5-190°
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[solubility ]

DMSO (Slightly), Methanol (Slightly), Water (Slightly)
[form ]

Solid
[color ]

White to Off-White
[Major Application]

pharmaceutical (small molecule)
[InChI]

1S/C21H28N2O5.ClH/c1-23(2)10-11-28-17-8-6-15(7-9-17)14-22-21(24)16-12-18(25-3)20(27-5)19(13-16)26-4;/h6-9,12-13H,10-11,14H2,1-5H3,(H,22,24);1H
[InChIKey]

WIIZEEPFHXAUND-UHFFFAOYSA-N
[SMILES]

[Cl-].N(CCOc1ccc(cc1)CNC(=O)c2cc(c(c(c2)OC)OC)OC)(C)C.[H+]
Safety DataBack Directory
[WGK Germany ]

3
[HS Code ]

2924296000
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Resp. Sens. 1
Skin Sens. 1
Hazard InformationBack Directory
[Originator]

Tigan,Beecham,US,1973
[Uses]

antiemetic
[Manufacturing Process]

To 122 grams (1 mol) of p-hydroxybenzaldehyde in 1 liter of chlorobenzene were added 66 grams (1.04 mols) of sodium methoxide (85%) and 108 grams (1 mol) of 2-dimethylaminoethyl chloride. The mixture was stirred and refluxed for 15 hours, then cooled and the precipitated sodium chloride filtered off. The filtrate was concentrated at steam temperature under water vacuum and the residual oil was fractionated in high vacuum, to give 4-(2- dimethylaminoethoxy)benzaldehyde, BP2.2145°C.
Two teaspoons of Raney nickel catalyst were added to a solution of 65.6 grams (0.34 mol) of 4-(2-dimethylaminoethoxy)benzaldehyde in 300 ml of 10% ammoniacal ethanol. The mixture was hydrogenated at 80°C and a pressure of 1,000 psi. The catalyst was filtered off, the volatiles were distilled off and the residual oil was fractionated in high vacuum, to obtain 4-(2- dimethylaminoethoxy)benzylamine, BP0.3120° to 123°C.
To 9.7 grams (0.05 mol) of 4-(2-dimethylaminoethoxy)benzylamine, dissolved in 100 ml of acetonitrile, was added all at once 12 grams (0.051 mol) of 3,4,5-trimethoxybenzoyl chloride, dissolved in 75 ml of acetonitrile. The mixture was stirred and refluxed for 8 hours, and then cooled. The crystalline solid, which had formed, was filtered off, washed with acetonitrile and recrystallized from acetonitrile, to give 4-(2-dimethylaminoethoxy)-N-(3,4,5- trimethoxybenzoyl)benzylamine hydrochloride, MP 185° to 186°C.
[Brand name]

Tigan (King).
[Therapeutic Function]

Antinauseant
Spectrum DetailBack Directory
[Spectrum Detail]

TRIMETHOBENZAMIDE HYDROCHLORIDE(554-92-7)1HNMR
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